The Asking Dilemma


I write about listening and asking often because they are two of the most powerful tools a leader can use for strengthening work relationships; they are also underappreciated. Are they too simple? Perhaps that’s one of the reasons for pushback. But there are others worth exploring; especially in the realm of asking (inquiry) instead of telling.

Most leaders that I work with could insert more inquiry into their leadership style. Inquiry (or more appropriately, asking questions to coach others to come up with their own solutions) is a central skill set for helping others to develop.

I work almost exclusively with mid- to upper- management in organizations. These are the people who’ve had many years of experience managing others, which makes it even more puzzling that the skill of inquiry hasn’t been accepted and valued. Let’s see if we can respond the excuses leaders have for avoiding this skill. Is it possible you are resisting for the same reasons?

“Asking questions isn’t my style”. There is no reason why asking questions can’t be part of your style. Yes, it takes courage to do something different, and it’s hard at first, but gets easier with practice. What have you got to lose? Next time you have someone come into your office with a problem that they want to drop in your lap for solving, turn it around. Ask them:  

What have you thought of so far?

What have you seen others do?

What do you think might work?

What are you willing to try?

“Asking takes longer than telling”. This is true. It takes time for people to come up with answers, and we need to be patient enough to let them think. Is it possible that, by asking and allowing your staff to come up with their own answers that they might learn something in the thought process? Is it possible that their answers might be more creative than anything you could come up with yourself?

“My staff doesn’t know enough to have the answers”. Oh boy, there are lots of responses to that. It takes a lot of courage to accept answers that aren’t yours. By asking, you are helping them to learn how to learn. If you aren’t asking, how do you know that they don’t know enough (wouldn’t it be great if you were surprised)?

“My employees want me to tell them the answers”. Sure, there might be some resistance as you change to incorporating more inquiry into your leadership style. Hang in there. Your best employees will appreciate the challenge of figuring stuff out and your less-than-best employees may never get it (and then you have a decision to make).

Hmmm…….I wonder if it’s a lack of courage that keeps you from asking (that’s a challenge, by the way)? What’s really keeping you from trying to incorporate more inquiry into your leadership?


I am a former executive in a Fortune 100 company. I have owned and operated an executive coaching firm since 2003 called Aspire Collaborative Services LLC. We partner with great leaders to help them become even greater at developing, improving, and sustaining relationships with the people who are essential to their success. This blog is for leaders and those who help them to be more intentional about relationships at work. My top personal values include respect for others, kindness, compassion, collaboration and gratitude. I work very hard at practicing my values daily and when I don’t succeed, I practice some more. I am married with two wonderful daughters and two spoiled pugs.

8 comments on “The Asking Dilemma

  1. Excellent post Mary Jo. Although I wonder if a more basic question must be asked of the leaders you’ve described here: If you’re not actively encouraging the development of your people, then why have you assumed the role of “leader” in the first place?

  2. Great question Andy. I find “interesting” the number of managers who don’t consider developing their employees part of their job. Sadly, it often isn’t something that THEIR managers think is important. Our organizations could be so much stronger if every manager/leader prepared others to also lead!

  3. I love the discipline of asking rather than telling. I love to be asked to think by my own boss, and I love to see the wheels turning when the people who report to me are using their brains and tapping into their innate wisdom. The best mentor to me in this approach is Max DePree.

  4. Welcome, Shirley. Your comments are one of the best testimonials to the power of inquiry out there. I agree, yet sometimes feel alone in loving the questions more than the answers. Do you think that people just need to experience “tapping into their innate wisdom” more to appreciate it like you and I do?

    P.S. I am also a big fan of Max DePree!

  5. I’ve seen those leaders before. I’ve even been most of them at one time or another.

    One thing I would add. Inquiry is important and most of us don’t do enough. But it has to be paired with listening that results in some action to be effective.

  6. Thanks for being humble, Wally. I have been most of them too. How true it is that inquiry must be paired with listening. Without listening, seems to me, its only probing.

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